Potassium Iodide → Ethyl 4-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridinecarboxylate

HRID 1828427ノート

反応式

HRID 1828427 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=1.Cl[CH2:14][C:15]1[S:16][CH:17]=[C:18]([CH:20]([CH3:22])[CH3:21])[N:19]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:20]([C:18]1[N:19]=[C:15]([CH2:14][O:1][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=2)[S:16][CH:17]=1)([CH3:22])[CH3:21]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 220637012-(Chloromethyl)-4-isopropylthiazoleHCID 178469317HCID 178469317、化合物

生成物 1

HCID 22063568Ethyl 4-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridinecarboxylate収率 46.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
110 °C

実験手順

Ethyl 4-hydroxy-2-pyridinecarboxylate (19.5 g, 0.057 mol) dissolved in dimethylformamide (200 ml) was added with a solution of 2-(chloromethyl)-4-isopropyl-1,3-thiazole (11 g, 0.063 mol) in dimethylformamide (150 ml). The mixture was added with potassium iodide (9.5 g) and potassium carbonate (12 g) at room temperature, then heated to 110° C. and stirred for 1 hour. The reaction solution was returned to room temperature, and the solvent was evaporated under reduced pressure. The residue was diluted with chloroform and washed with water. The resulting organic layer was washed with saturated brine, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (chloroform) to obtain 8.049 g (46%) of the title compound.

後処理

  1. customwas returned to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was diluted with chloroform
  4. washwashed with water
  5. washThe resulting organic layer was washed with saturated brine
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (chloroform)

出典と根拠

ORDレコード
ord-1abc6c72148649ca874c2d0ccc4b616f
出典データセット
uspto-grants-2006_06
特許番号
US07056917B2

反応ノート

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